Pimple's trade and wealth grew, and he began to buy up land and property across the Shire, from inns and mills to farms and more plantations. Eventually, he sent so much of the Shire's produce away into the south that its people began to suffer hardship. Then, Lotho's Ruffians came out of the southern lands to quell the Shire-hobbits' complaints, and Pimple took the title of Chief Shirriff.

Eventually Saruman himself arrived in the Shire, though the hobbits had no idea of his history or nature, knowing him only by the name his servants used, 'Sharkey'. At about this time Lotho Pimple fell out of view, and it was thought that he was being held prisoner by Sharkey at his headquarters, Bag End. The truth was far worse: Saruman's servant Wormtongue had stabbed the self-appointed Chief Shirriff in his sleep. So the hobbit who had tried to take control of the Shire came to a grisly and untimely end.